8-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene → 8-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decane

HRID 2264283Notes

Reaction equation

HRID 2264283 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH:11]=1>CO.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:11][CH2:12][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:18][CH2:19]1

Participants

5

Reactant 1

HCID 574243608-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 574243618-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene in methanol (240 mL) and ethyl acetate (5 mL) was treated with 10% palladium on carbon (7.0 g) and stirred under an atmosphere of hydrogen gas (40 psi) overnight. The reaction mixture was filtered over Celite. The filtrate was concentrated and chromatographed (silica gel, gradient 5-7% ethyl acetate in hexane) to yield the title compound.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. concentrationThe filtrate was concentrated
  3. customchromatographed (silica gel, gradient 5-7% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b19d73fed1944897b28758c1d1799f59
Source dataset
uspto-grants-2010_12
Patent number
US07855206B2

Reaction notes

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